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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 229 Cottages in Old Saybrook with updated reviews, rates, and availability.

Lakeside cottage overhanging the water, beautiful window views across the lake
Outdoor dining

Lakeside cottage overhanging the water, beautiful window views across the lake

9.8 out of 10, Exceptional, (201)
"Had an absolutely fantastic time. Great being close to the water. Will definitely be back once it gets warmer."
The price is AED 841
AED 1,562 total
includes taxes & fees
19 May - 20 May
Lakeside cottage overhanging the water, beautiful window views across the lake
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Lakeside cottage ON the water with beautiful views up the lake!
Pool

Lakeside cottage ON the water with beautiful views up the lake!

9.8 out of 10, Exceptional, (173)
"We came for a couple of days for my son’s birthday and even though it was winter with the lake frozen over, there were still many options to keep us occupied all while staying warm and cozy. Definitely want to make a trip back for the summer!"
The price is AED 694
AED 1,368 total
includes taxes & fees
21 May - 22 May
Lakeside cottage ON the water with beautiful views up the lake!
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
Private Guest House w/ Deck + Spectacular Views!
Property grounds

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (26)
"Great place. Great host"
Private Guest House w/ Deck + Spectacular Views!
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (25)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 459
AED 728 total
includes taxes & fees
15 May - 16 May
1-bedroom cottage with Grove Beach 🏖️ access.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"Property is charming, beautifully decorated, clean. Host was very responsiveand even shared produce from her lovely garden! We hope to return."
The gardners Cottage 1 mile from long Island Sound - pet friendly
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (20)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
Orient Village — Historic Bayfront Cottage — 2025 Season
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Miscellaneous

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (91)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (108)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"The location and property were perfect for our stay. Homeowner was very accommodating. Can’t wait to go back!!!!"
Charming Old Lyme Cottage, Steps to Private Beach!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.6 out of 10, Exceptional, (4)
"Had a great stay!"
Charming Westbrook Cottage, Steps to Private Beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Waterfront! Charming 4BR Cottage on the Niantic River!
Property grounds

Waterfront! Charming 4BR Cottage on the Niantic River!

9.6 out of 10, Exceptional, (59)
"We enjoyed this lovely old home and had a lot of fun kayaking and seeing the sights in the area. Amy was a wonderful host."
Waterfront! Charming 4BR Cottage on the Niantic River!
Beach duplex—2 full homes with private access, backyard, and ocean views!
Beach nearby, sun loungers

Beach duplex—2 full homes with private access, backyard, and ocean views!

10.0 out of 10, Exceptional, (15)
" Very clean, plenty of room for multi generational family and the beach was very relaxing. Will stay again."
Beach duplex—2 full homes with private access, backyard, and ocean views!
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby, sun loungers, beach towels

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (25)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Old Saybrook

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
Interior

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (128)
"We loved our stay!"
The price is AED 1,499
AED 2,749 total
includes taxes & fees
13 May - 14 May
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
adorable ranch in beach community
Beach nearby

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
The price is AED 404
AED 1,234 total
includes taxes & fees
18 May - 19 May
adorable ranch in beach community
Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (14)
"Quite and intimate..great great time Definitely coming again!!!"
The price is AED 422
AED 634 total
includes taxes & fees
12 May - 13 May
Postcard Cabins Machimoodus
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.